It's fairly easy now to run headless from scratch with a Raspberry Pi.

One area that might have an issue though is debugging issues with devices that have been added to the Raspberry Pi. Often you get indication of these problems in the messages that scroll through during boot.

Are these messages echoed anywhere - to a log - or are they only available if you connect a monitor during boot?

The title of this question sounds terrifying.
– JivingsJul 5 '12 at 13:00

1

if you are using raspbrian (you probably are), then installing bootlogd will add boot logs. I did not have any boot logs on my laptop running debian-x86, until I installed this package.
– ctrl-alt-delorJun 28 '14 at 23:07

I really need to get one of those! My remote headless Pi just failed to start up properly after a full update. Kind of ugly if you cannot ssh into the system any more to check the logs.
– Ghanima♦Apr 20 '15 at 19:26

But what software do you use on your other computer to connect?
– MikeSchinkelSep 24 '16 at 2:23

1

@MikeSchinkel, Any terminal emulator: on linux I usually use minicom or screen. putty on windows
– John La RooySep 25 '16 at 10:36